Holiday rentals in Southend Chalkwell Beach

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Top-rated holiday rentals in Southend Chalkwell Beach

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Apartment
5 out of 5 average rating, 12 reviews

Apartment heart of Leigh on Sea. 2 double bedrooms

A stunning 2 double bedroom apartment in the centre of Leigh. Up to 4 guests. Be in the heart of the shops, cafes, bars & amazing restaurants. Everything is a couple of minutes walk! From the beach, bus stop train station & The Broadway. 12 mins to the airport. There are 2 modern double bedrooms, sleek, clean & modern bathroom and kitchen as well as spacious living area to enjoy. Situated above a designer shop overlooking the fabulous independent shops of Leigh. No stags, no pets & no smoking

Guest favourite
A dining area features a round table set for four, accompanied by stylish chairs. Natural light fills the space through a nearby window. A decorative mirror and woven pendant light add inviting elements to the warm, neutral tones of the room.
Cottage
4.88 out of 5 average rating, 48 reviews

Luxury Heritage Cottage in the Heart of Old Leigh

A beautifully refurbished 2 Bedroom Heritage Fisherman's Cottage with historic charm & modern comfort. This cosy cottage in the heart of Old Leigh offers stunning sea views & a warm, stylish retreat. Perfect for couples or small families. 🧺 Welcome basket 🌊 Sea views 🧳 Long stays welcome 🏖️Waterside Balcony ❤️ Ideal for romantic getaways & family breaks 💻Excellent Wifi 🛁 2 Bathrooms Steps from Leigh-on-Sea’s coastal walks, boutique shops & renowned seafood spots-all within easy reach.

Top guest favourite
A serene view of the sea features multiple sailboats gently bobbing on the calm water. The scene is set against a clear blue sky, creating a peaceful atmosphere that invites relaxation and enjoyment of the coastal surroundings.
Home
4.88 out of 5 average rating, 99 reviews

Stunning sea views. Local for beach & eateries

Situated in Leigh on Sea, a stunning 2 bedroom maisonette a stones throw from the beach. You have clear sea views from both bedrooms, kitchen and sitting room There is a private balcony leading from both bedrooms and also from the sitting/dinning room. All balconies have seating to allow you to relax and read a book or have your morning cuppa. Whichever way you walk you will find tasty restaurants and cute coffee bars within minutes. Available on the beach-sup lessons, photography & yoga.

Top guest favourite
A spacious living area features plush green sofas arranged around a central coffee table. A large decorative mirror reflects light, while a modern chandelier hangs above. Natural light pours in through large windows, dressed with elegant shades.
Home
5 out of 5 average rating, 127 reviews

Amazing house with sea views in Leigh-on-Sea

Amazing character 3 storey house dating from 1860’s with sea views, modernised and expanded in 2009 to provide 3 king size luxury bedrooms, (2 with en-suite) 1 large dressing room, 1 large family bathroom with bath, sink, large walk on shower and double sinks and large open plan ground floor set over two levels with large luxury sitting room, stepping down to open plan dining area, kitchen with central island unit and rear seating area with bi-fold doors opening onto a luxury garden area.

Guest favourite
An elegantly designed bedroom features a spacious super king bed adorned with soft linens and stacked towels. A freestanding bath is positioned nearby, complemented by wooden wall accents. A cozy robe hangs in the background, while soft lighting contributes to a serene atmosphere.
Farm stay
4.98 out of 5 average rating, 386 reviews

Exclusive retreat on a private lake

Enjoy a truly unique stay in this exclusive lodge. Situated on its own private lake, you will have everything you need to enjoy a blissful retreat with award winning country pubs such as The Dog & Pickle only a walk away. Please note: 1. We are strictly a minimum of two night stays. 2. We can only accept infants under 6 months old. 3. There is no swimming or paddle boarding allowed in the lake. NEW FOR 2026 - The Wellness Deck Sauna, Cold Plunge & outdoor shower, ready for use now!

Top guest favourite
A balcony view is captured through bi-fold glass doors, featuring a small round table and two folding chairs. A decorative pumpkin sits at the center, with panoramic sea views of the estuary and boats in the distance, framed by a serene sunset.
Apartment
4.99 out of 5 average rating, 430 reviews

Estuary Views Penthouse with Private Parking

A Beachfront Coastal Retreat with private driveway parking & situated in the sort after area Thorpe Bay. Boasting unspoilt Panoramic Sea Views. Central to Blue Flag Beaches, 2 mins from award winning restaurants, superb location for coastal walks, watching the seabirds & a short walk to the longest Pier in the world. Re-Designed with Bi-Folding Glass doors, bringing the Outside Inside. Intricately Designed embracing tiny details that define our property for a Luxury & cosy stay.

Guest favourite
An open living area features a modern gray sofa, sleek cabinetry, and a wall-mounted television. Large windows offer views of the surrounding landscape. The wooden flooring, designed in a herringbone pattern, complements the light wood paneling and cabinetry throughout the space.
Barn
4.87 out of 5 average rating, 120 reviews

Oak Lodge @ The Oaks Retreat

This memorable place is anything but ordinary. It is The Oaks Retreat, WINNER of the Paris Design awards 2024 'best hospitality interior', an architecturally inspired bespoke woodland Airbnb located in the seaside town of Whitstable. The Oak Lodge offers 2 king size bedrooms fully customized with high-end finishes which to need to be seen in person to be fully appreciated. Our Wellness area is equipped with a log burning sauna, a cold plunge and outdoor shower.

Guest favourite
A cozy bedroom features a spacious bed with neutral bedding and decorative pillows. Two bedside lamps provide soft lighting, and framed artwork is displayed above the bed. Light-colored walls and wooden flooring contribute to a fresh and clean ambiance.
Flat
4.88 out of 5 average rating, 96 reviews

Cozy brand new serviced apartment

A beautifully designed one bedroom apartment, recently refurbished to a high standard. Dream Yard is situated in the heart of the vibrant Hamlet Court Road with immediate access to cafes, restaurants and shops. Less than five minutes to the Westcliff train station and less than 10 min to the beach. The flat is self catered comprising bedroom, shower, kitchen and living room with access to the Chéri’s Cafe. Guests enjoy 10% discount on food.

Top guest favourite
Bungalow
4.97 out of 5 average rating, 105 reviews

Luxury Spa Retreat: Sauna & Hot Tub

Escape to our exclusive gated spa retreat, nestled on 5.5 acres of serene countryside in picturesque Fawkham, Kent. This private and tranquil haven offers breathtaking views of rolling hills, perfect for relaxation. Unwind in the luxurious sauna, steam room, or hot tub, soaking in the peace after exploring local attractions. Just minutes from Brands Hatch, our retreat blends seclusion with convenience, your ultimate quiet getaway awaits.

Guest favourite
A cozy bedroom is presented with a double bed featuring an ornate headboard. Two cushions in navy blue rest on the crisp white linens. A piece of wall art depicting vibrant lips adds a pop of color. A flat-screen TV is mounted on the wall opposite the bed.
Flat
4.97 out of 5 average rating, 196 reviews

Lovely studio for two in central Leigh on Sea

This is a very calm space decorated in F&B elephants breath paint with contrasting furnishings. A double bed + a sofa bed + travel cot. Cooking facilities, dining table table & 2 chairs. A microwave is situated in the utility room on the landing outside the studio door. Very nice shower room It’s ideal as a compact living space to use when visiting relatives or just on a break in lovely Leigh on Sea. No outside space is available.

Top guest favourite
An open-plan kitchen and dining area is visible through bifold doors, creating a seamless connection to the outdoor courtyard. Tall bar stools align a light wood dining table, with soft seating arranged around a low table adorned with snacks and glasses. Potted greenery enhances the inviting space.
Home
4.96 out of 5 average rating, 53 reviews

Stunning house in the heart of Leigh-On-Sea

Beautifully restored 3 bedroom detached house in the very heart of the vibrant and trendy Leigh on Sea Broadway moments from the bars, boutiques, galleries and coffee shops and just a short walk to the sea. A collaboration between Mother and Daughter, Interior Designer, Nathalie Brandajs and Artist, Caron Brandajs, who transformed and beautifully styled this period property.

Guest favourite
A cozy living area features a brown leather chesterfield sofa adorned with decorative pillows. A wooden coffee table sits in the center, surrounded by a plush area rug. Framed artwork decorates the walls, and lush plants add a touch of greenery to the space.
Home
4.92 out of 5 average rating, 104 reviews

Stunning Cottage in the Heart of Old Leigh

Welcome to our delightful 3-bedroom cottage, perfectly nestled in the picturesque centre of Old Leigh. This charming retreat offers a blend of comfort and stunning sea views, making it the ideal getaway for families or groups of friends. Professionally managed by Pass The Keys, this homes has excellent Wifi

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